Indole-derived arynes and their Diels-Alder reactivity with furans.

@article{Buszek2007IndolederivedAA,
  title={Indole-derived arynes and their Diels-Alder reactivity with furans.},
  author={Keith R. Buszek and Diheng Luo and Mikhail V. Kondrashov and Neil C. M. Brown and David VanderVelde},
  journal={Organic letters},
  year={2007},
  volume={9 21},
  pages={
          4135-7
        }
}
Arynes derived from any position of the ubiquitous indole nucleus are unknown. We have now provided the first evidence for the formation and trapping of the 4,5-, 5,6-, and 6,7-indolynes. A series of o-dihalo indoles (Cl, Br, F) were synthesized and reacted under metal-halogen exchange conditions to give Diels-Alder cycloadducts in high yield with furan. The use of an excess of tert-butyllithium resulted in the rearrangement of the initially formed cycloadduct; however, employing only a slight… CONTINUE READING
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